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Abstract

While much is known about the hormones of vertebrates, knowledge of the hormones of invertebrates is far less complete. However, the chemistry of the molting hormones and the juvenile hormones of insects has made surprisingly rapid advances during the past few years and has now become a subject of research which is attracting the interest of both chemists and biologists. This review article is an attempt to summarize recent developments in our knowledge regarding the chemistry, synthesis and metabolism of the arthropod molting hormones, but will in the main exclude consideration of biological properties which have been frequently the object of excellent reviews (71).

Keywords

Juvenile Hormone Methyl Ketone Tetrahedron Letter Molting Hormone Positive Cotton Effect 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    Becker, E.: Über Versuche zur Anreicherung und physiologischen Charakterisierung des Wirkstoffs der Puparisierung. Biol. Zbl. 61, 360 (1941).Google Scholar
  2. 2.
    Becker, E. und E. Plagge: Über das die Pupariumbildung auslösende Hormon der Fliegen. Biol. Zbl. 59, 326 (1939).Google Scholar
  3. 3.
    Burdette, W.J.: Changes in Titer of Ecdysone in Bombyx mori during Metamorphosis. Science 135, 432 (1962).CrossRefGoogle Scholar
  4. 4.
    Burdette, W.J. and M.W. Bullock: Ecdysone: Five Biologically Active Fractions from Bombyx. Science 140, 1311 (1963).CrossRefGoogle Scholar
  5. 5.
    Butenandt, A. und P. Karlson: Über die Isolierung eines Metamorphose-Hormons der Insekten in kristallisierter Form. Z. Naturforsch. 9b, 389 (1954).Google Scholar
  6. 6.
    Faux, A., D.H.S. Horn, E.J. Middleton, H.M. Fales and M.E. Lowe: Moulting Hormones of a Crab during Ecdysis. Chem. Commun. 1969, 175.Google Scholar
  7. 7.
    Fraenkel, G.: Hormone Causing Pupation in the Blowfly Calliphora erythrocephala. Proc. Roy. Soc. London Ser. B 118, 1 (1935).CrossRefGoogle Scholar
  8. 8.
    Furlenmeier, A., A. Fürst, A. Langemann, G. Waldvogel, P. Hocks, U. Kerb and R. Wiechert: The Synthesis of Ecdysone. Experientia 22, 573 (1966).CrossRefGoogle Scholar
  9. 9.
    Furlenmeier, A., A. Fürst, A. Langemann, G. Waldvogel, P. Hocks, U. Kerb and R. Wiechert: Zur Synthese des Ecdysons. Helv. Chim. Acta 50, 2387 1967).CrossRefGoogle Scholar
  10. 10.
    Furlenmeier, A., A. Fürst, A. Langemann, G. Waldvogel, U. Kerb, P. Hocks und R. Wiechert: Zur Synthese des Ecdysons. Synthesen von 2β,3β,14α-Trihydroxy-6-keto-Δ 7-A/B-cis-Steroiden. Helv. Chim. Acta 49, 1591 (1966).CrossRefGoogle Scholar
  11. 11.
    Galbraith, M.N. and D.H.S. Horn: An Insect-Moulting Hormone from a Plant. Chem. Commun. 1966, 905.Google Scholar
  12. 12.
    Galbraith, M.N. and D.H.S. Horn: Insect Moulting Hormones: Crustecdysone (20-Hydroxyecdysone) from Podocarpus elatus. Austral. J. Chem. 22, 1045 (1969).CrossRefGoogle Scholar
  13. 13.
    Galbraith, M.N. and D.H.S. Horn: unpublished results.Google Scholar
  14. 14.
    Galbraith, M.N., D.H.S. Horn, P. Hocks, G. Schulz and H. Hoffmeister: The Identity of the 20-Hydroxy-Ecdysones from Various Sources. Naturwiss. 54, 471 (1967).CrossRefGoogle Scholar
  15. 15.
    Galbraith, M.N., D.H.S. Horn, E.J. Middleton and R.J. Hackney: Structure of Deoxycrustecdysone, a Second Crustacean Moulting Hormone. Chem. Commun. 1968, 83.Google Scholar
  16. 16.
    Galbraith, M.N., D.H.S. Horn, E.J. Middleton and R.J. Hackney: A Silyl Ether as a Protecting Group in the Synthesis of an Isomer of Ecdysone, 2oS-Hydroxy-22-deoxyecdysone. Chem. Commun. 1968, 466.Google Scholar
  17. 17.
    Galbraith, M.N., D.H.S. Horn, E.J. Middleton and R.J. Hackney: The Structure of Podecdysone B, a New Phytoecdysone. Chem. Commun. 1969, 402.Google Scholar
  18. 18.
    Galbraith, M.N., D.H.S. Horn, E.J. Middleton and R.J. Hackney: Moulting Hormones of Insects and Crustaceans: The Synthesis of 2-Deoxy-3-epicrustecdysone. Austral. J. Chem. 22, 1059 (1969).CrossRefGoogle Scholar
  19. 19.
    Galbraith, M.N., D.H.S. Horn, E.J. Middleton and R.J. Hackney: Moulting Hormones of Insects and Crustaceans: The Synthesis of 22-Deoxycrustecdysone. Austral. J. Chem. 22, 1517 (1969).CrossRefGoogle Scholar
  20. 20.
    Galbraith, M.N., D.H.S. Horn, E.J. Middleton, J.A. Thomson, J.B, Siddall and W. Hafferl: The Catabolism of Crustecdysone in the Blowfly Calliphora stygia. Chem. Commun. 1969, 1134.Google Scholar
  21. 21.
    Galbraith, M.N., D.H.S. Horn, Q.N. Porter and R.J. Hackney: Structure of Podecdysone A, a Steroid with Moulting Hormone Activity from the Bark of Podocarpus elatus R. Br. Chem. Commun. 1968, 971.Google Scholar
  22. 22.
    Galbraith, M.N., D.H.S. Horn, J.A. Thomson, G.J. Neufeld and R.J. Hackney: Insect Moulting Hormones: Crustecdysone in Calliphora. J. Insect Physiol. 15, 1225 (1969).CrossRefGoogle Scholar
  23. 23.
    Gilbert, L.I.: Hormones Controlling Reproduction and Molting in Invertebrates. Comparative Endocrinology, Vol. II. p. 1. New York: Academic Press. 1963.Google Scholar
  24. 24.
    Hampshire, F. and D.H.S. Horn: Structure of Crustecdysone, a Crustacean Moulting Hormone. Chem. Commun. 1966, 37.Google Scholar
  25. 25.
    Harrison, I.T., J.B. Siddall and J.H. Fried: Synthetic Studies on Insect Hormones. III. An Alternative Synthesis of Ecdysone and 22-Isoecdysone. Tetrahedron Letters 1966, 3457.Google Scholar
  26. 26.
    Heftmann, E., H.H. Sauer and R.D. Bennett: Biosynthesis of Ecdysterone from Cholesterol by a Plant. Naturwiss. 55, 37 (1968).CrossRefGoogle Scholar
  27. 27.
    Heinrich, G. und H. Hoffmeister: Ecdyson als Begleitsubstanz des Ecdysterons in Polypodium vulgare L. Experientia 23, 995 (1967).CrossRefGoogle Scholar
  28. 28.
    Heinrich, G. und H. Hoffmeister: 5β-Hydroxyecdysteron, ein Pflanzensteroid mit Häutungshormonaktivitat aus Polypodium vulgare L. Tetrahedron Letters 1968, 6063; cf. Addendum: Ibid. 1969, No. 30, ii.Google Scholar
  29. 29.
    Hikino, H., S. Arihara and T. Takemoto: Ponasteroside A, a Glycoside of Insect Metamorphosing Substance from Pteridium aquilinum var. latiusculum: Structure and Absolute Configuration. Tetrahedron 25, 3909 (1969).CrossRefGoogle Scholar
  30. 30.
    Hikino, H., Y. Hikino, K. Nomoto and T. Takemoto: Cyasterone, an Insect Metamorphosing Substance from Cyathula capitata: Structure. Tetrahedron 24, 4895 (1968).CrossRefGoogle Scholar
  31. 31.
    Hikino, H., Y. Hikino and T. Takemoto: Synthesis of Rubrosterone, a Metabolite of Insect-Moulting Substances from Achyranthes rubrofusca. Tetrahedron Letters 1968, 4255.Google Scholar
  32. 32.
    Hikino, H., Y. Hikino and T. Takemoto: Rubrosterone, a Metabolite of Insect Metamorphosing Substance from Achyranthes rubrofusca: Synthesis. Tetrahedron 25, 3389 (1969).CrossRefGoogle Scholar
  33. 33.
    Hiking, H., H. Jin and T. Takemoto: unpublished results.Google Scholar
  34. 34.
    Hikino, H., T. Kohama and T. Takemoto: Biosynthesis of Ponasterone A, an Insect-Moulting Substance from Podocarpus macrophyllus. Chem. Pharm. Bull. (Japan) 17, 415 (1969).CrossRefGoogle Scholar
  35. 35.
    Hikino, H., T. Kohama and T. Takemoto: Biosynthesis of Ponasterone A and Ecdysterone from Cholesterol in Podocarpus macrophyllus. Phytochem. 9, 367 (1970).CrossRefGoogle Scholar
  36. 36.
    Hikino, H., K. Nomoto and T. Takemoto: Structure of Sengosterone, a Novel C29 Insect-Moulting Substance from Cyathula capitata. Tetrahedron Letters 1969, 1417.Google Scholar
  37. 37.
    Hikino, H., K. Nomoto and T. Takemoto: unpublished results.Google Scholar
  38. 38.
    Hocks, P., A. Jäger, U. Kerb, R. Wiechert, A. Furlenmeier, A. Fürst, A. Langemann und G. Waldvogel: Synthetische Steroide mit Häutungshormonaktivität. Angew. Chem. 78, 680 (1966).CrossRefGoogle Scholar
  39. 39.
    Hocks, P., U. Kerb, R. Wiechert, A. Furlenmeier und A. Fürst: Die Synthese des Rubrosterons. Tetrahedron Letters 1968, 4281.Google Scholar
  40. 40.
    Hocks, P., G. Schulz und P. Karlson: Die Struktur des β-Ecdysons. Naturwiss. 54, 44 (1967).CrossRefGoogle Scholar
  41. 41.
    Hocks, P. and R. Wiechert: 20-Hydroxy-Ecdyson, Isoliert aus Insekten. Tetrahedron Letters 1966, 2989.Google Scholar
  42. 42.
    Hoffmeister, H. und H.-F. Grützmacher: Zur Chemie des Ecdysterons. Tetrahedron Letters 1966, 4017.Google Scholar
  43. 43.
    Hoffmeister, H., H-.F. Grützmacher und K. Dünnebeil: Untersuchungen über die Struktur und biochemische Wirkung von Ecdysteron. Z. Naturforsch. 22b, 66 (1967).Google Scholar
  44. 44.
    Hoffmeister, H., G. Heinrich, G.B. Staal und W.J. van der Burg: Über das Vorkommen von Ecdysteron in Eiben. Naturwiss. 54, 471 (1967).CrossRefGoogle Scholar
  45. 45.
    Hoffmeister, H., K. Nakanishi, M. Koreeda and H.Y. Hsu: The Moulting Hormone Activity of Ponasterones in the Calliphora Test. J. Insect Physiol. 14. 53 (1968).CrossRefGoogle Scholar
  46. 46.
    Hoffmeister, H. und C. Rufer: Zur Chemie des Ecdysons, IV. Farbreaktionen von gesättigten und ungesättigten Steroidketonen. Chem. Ber. 98, 2376 (1965).CrossRefGoogle Scholar
  47. 47.
    Hoffmeister, H., C. Rufer, H.H. Keller, H. Schairer und P. Karlson: Zur Chemie des Ecdysons, III. Vergleichende spektrometrische Untersuchungen an α,β-ungesättigten Steroidketonen. Chem. Ber. 98, 2361 (1965).CrossRefGoogle Scholar
  48. 48.
    Hoppe, W. und R. Huber: Zur Chemie des Ecdysons, II. Bestimmung des Sterin-Skeletts und seiner Orientierung mit diffuser Röntgenstreuung in Kristallen von Ecdyson. Chem. Ber. 98, 2353 (1965).CrossRefGoogle Scholar
  49. 49.
    Hora, J., L. Lábler, A. Kasal, V. Černý, F. Šorm and K. Sláma: Molting Deficiencies Produced by some Sterol Derivatives in an Insect (Pyrrhocoris apterus L.). Steroids 8, 887 (1966).CrossRefGoogle Scholar
  50. 50.
    Hori, M.: Automatic Column Chromatographic Method for Insect-Moulting Steroids. Steroids 14, 33 (1969).CrossRefGoogle Scholar
  51. 51.
    Horn, D.H.S.: Moulting Hormones of Crustaceans, unpublished work.Google Scholar
  52. 52.
    Horn, D.H.S., S. Fabbri, F. Hampshire and M.E. Lowe: Isolation of Crustecdysone (20 R-Hydroxyecdysone) from a Crayfish (Jasus lalandei H. Milne-Edwards). Biochem. J. 109, 399 (1968).Google Scholar
  53. 53.
    Horn, D.H.S., E.J. Middleton and J.A. Thomson: unpublished results.Google Scholar
  54. 54.
    Horn, D.H.S., E.J. Middleton, J.A. Wunderlich and F. Hampshire: Identity of the Moulting Hormones of Insects and Crustaceans. Chem. Commun. 1966, 339.Google Scholar
  55. 55.
    Huber, R. und W. Hoppe: Zur Chemie des Ecdysons, VII. Die Kristall-und Molekülstruktur Analyse des Insektenverpuppungshormons Ecdyson mit der automatisierten Faltmolekülmethode. Chem. Ber. 98, 2403 (1965).CrossRefGoogle Scholar
  56. 56.
    Hüppi, G. and J.B. Siddall: Synthetic Studies on Insect Hormones. V. The Synthesis of Crustecdysone (20-Hydroxyecdysone). J. Amer. Chem. Soc. 89, 6790 (1967).CrossRefGoogle Scholar
  57. 57.
    Hüppi, G. and J.B. Siddall: Synthetic Studies on Insect Hormones VI. The Synthesis of Ponasterone A and its Stereochemical Identity with Crustecdysone. Tetrahedron Letters 1968, 1113.Google Scholar
  58. 58.
    Imai, S., S. Fujioka, E. Murata, K. Otsuka and K. Nakanishi: Structure of the Phytoecdysone, Ajugasterone B. Chem. Commun. 1969, 82.Google Scholar
  59. 59.
    Imai, S., S. Fujioka, E. Murata, Y. Sasakawa and K. Nakanishi: The Structures of Three Additional Phytoecdysones from Podocarpus macrophyllus, Makisterone B, C and D. Tetrahedron Letters 1968, 3887.Google Scholar
  60. 60.
    Imai, S., S. Fujioka, K. Nakanishi, M. Koreeda and T. Kurokawa: Extraction of Ponasterone A and Ecdysterone from Podocarpaceae and Related Plants. Steroids 10, 557 (1967).CrossRefGoogle Scholar
  61. 61.
    Imai, S., M. Hori, S. Fujioka, E. Murata, M. Goto and K. Nakanishi: Isolation of Four New Phytoecdysones, Makisterone A, B, C., D and the Structure of Makisterone A, a C28 Steroid. Tetrahedron Letters 1968, 3883.Google Scholar
  62. 62.
    Imai, S., E. Murata, S. Fujioka, M. Koreeda and K. Nakanishi: Structure of Ajugasterone C., a Phytoecdysone with an 11-Hydroxy-group. Chem. Commun. 1969, 546.Google Scholar
  63. 63.
    Imai, S., T. Toyosato, M. Sakai, Y. Sato, S. Fujioka, E. Murata and M. Goto: Screening Results of Plants for Phytoecdysones. Chem. Pharm. Bull. (Japan) 17, 335 (1969).CrossRefGoogle Scholar
  64. 64.
    Imai, S., T. Toyosato, M. Sakai, Y. Sato, S. Fujioka, E. Murata and M. Goto: Isolation of Cyasterone and Ecdysterone from Plant Materials. Chem. Pharm. Bull. (Japan) 17, 340 (1969).CrossRefGoogle Scholar
  65. 65.
    Jizba, J., V. Herout and F. Šorm: Isolation of Ecdysterone (Crustecdysone) from Polypodium vulgare L. Rhizomes. Tetrahedron Letters 1967, 1689.Google Scholar
  66. 66.
    Jizba, J., V. Herout and F. Šorm: Polypodine B — a Novel Ecdysone-like Substance from Plant Material. Tetrahedron Letters 1967, 5139.Google Scholar
  67. 67.
    Kaplanis, J.A., L.A. Tabor, M.J. Thomson, W.E. Robbins and T.J. Shortino: Assay for Ecdysone (Molting Hormone) Activity Using the House Fly, Musca domestica L. Steroids 8, 625 (1966).CrossRefGoogle Scholar
  68. 68.
    Kaplanis, J.N., M.J. Thompson, W.E. Robbins and B.M. Bryce: Insect Hormones: Alpha Ecdysone and 20-Hydroxyecdysone in Bracken Fern. Science 157, 1436 (1967).CrossRefGoogle Scholar
  69. 69.
    Kaplanis, J.N., M.J. Thompson, R.T. Yamamoto, W.E. Robbins and S.J. Louloudes: Ecdysones from the Pupa of the Tobacco Hornworm, Manduca sexta (Johannson). Steroids 8, 605 (1966).CrossRefGoogle Scholar
  70. 70.
    Karlson, P.: Biochemical Studies on Insect Hormones. Vitamins and Hormones 14, 227 (1956).CrossRefGoogle Scholar
  71. 71.
    Karlson, P. e. g., — Ecdyson das Häutungshormon der Insekten. Naturwiss. 53, 445 (1966).CrossRefGoogle Scholar
  72. 72.
    Karlson, P. and G. Hauser: Bildungsort und Erfolgsorgan des Puparisierungshormons der Fliegen. Z. Naturforsch. 8b, 91 (1953).Google Scholar
  73. 73.
    Karlson, P. and H. Hoffmeister: Zur Biologenese des Ecdysons, I. Umwandlung von Cholesterin in Ecdyson. Z. Physiol. Chem. 331, 298 (1963).CrossRefGoogle Scholar
  74. 74.
    Karlson, P., H. Hoffmeister, W. Hoppe und R. Huber: Zur Chemie des Ecdysons, I. Liebigs Ann. Chem. 662, 1 (1963).Google Scholar
  75. 75.
    Karlson, P., H. Hoffmeister, H. Hummel, P. Hocks und G. Spiteller: Zur Chemie des Ecdysons, VI. Reaktionen des Ecdysonmoleküls. Chem. Ber. 98, 2394 (1965).CrossRefGoogle Scholar
  76. 76.
    Karlson, P. and D.M. Skinner: Attempted Extraction of Crustacean Moulting Hormone from Isolated Y-Organs. Nature 185, 543 (1960) and earlier references cited therein.CrossRefGoogle Scholar
  77. 77.
    Kerb, U., P. Hocks, R. Wiechert, A. Furlenmeier, A. Fürst, A. Langemann und G. Waldvogel: Die Synthese des Ecdysons. Tetrahedron Letters 1966, 1387.Google Scholar
  78. 78.
    Kerb, U., G. Schulz, P. Hocks, R. Wiechert, A. Furlenmeier, A. Fürst, A. Langemann and G. Waldvogel: Zur Synthese des Ecdysons. Die Synthese des natürlichen Häutungshormons. Helv. Chim. Acta 49, 1601 (1966).CrossRefGoogle Scholar
  79. 79.
    Kerb, U., R. Wiechert, A. Furlenmeier und A. Fürst: Über eine Synthese des Crustecdysons (20-Hydroxyecdyson). Tetrahedron Letters 1968, 4277.Google Scholar
  80. 80.
    King, D.S. and J.B. Siddall: Conversion of α-Ecdysone to β-Ecdysone by Crustaceans and Insects. Nature 221, 955 (1969).CrossRefGoogle Scholar
  81. 81.
    Kobayashi, M., K. Nakanishi and M. Koreeda: The Moulting Hormone Activity of Ponasterones on Musca domestica (Diptera) and Bombyx mori (Lepidoptera). Steroids 9, 529 (1967).CrossRefGoogle Scholar
  82. 82.
    Kobayashi, M., T. Takemoto, S. Ogawa and N. Nishimoto: The Moulting Hormone Activity of Ecdysterone and Inokosterone Isolated from Achyranthis Radix. J. Insect Physiol. 13, 1395 (1967).CrossRefGoogle Scholar
  83. 83.
    Koreeda, M., K. Nakanishi, S. Imai, T. Tsuchiya and N. Wasada: Mass Spectrometric Studies of Ecdysone Derivatives. Mass Spectroscopy 17, 669 (1969).Google Scholar
  84. 84.
    Koreeda, M., N. Harada and K. Nakanishi: Interaction between Nonadjacent Benzoate Groups: an Extention of the Dibenzoate Chirality Rule. Chem. Commun. 1969, 548.Google Scholar
  85. 85.
    Koreeda, M., H. Moriyama, K. Nakanishi, S. Imai and T. Okauchi: Bioorganic Studies of the Eedysones. Symposium Papers of the 12th Symposium on the Chemistry of Natural Products, p. 129, Sapporo 1969.Google Scholar
  86. 86.
    Mori, H. and K. Shibata: Synthesis of Ecdysterone. Chem. Pharm. Bull. (Japan) 17, 1970 (1969).Google Scholar
  87. 87.
    Mori, H., K. Shibata, K. Tsuneda and M. Sawai: Synthesis of Ecdysone. I. A Novel Synthesis of 2β,3β-Dihydroxy Steroids. Chem. Pharm, Bull. (Japan) 15, 460 (1967).CrossRefGoogle Scholar
  88. 88.
    Mori, H., K. Shibata, K. Tsuneda and M. Sawai: Synthesis of Ecdysone. Chem. Pharm. Bull. (Japan) 16, 563 (1968).CrossRefGoogle Scholar
  89. 89.
    Mori, H., K. Shibata, K. Tsuneda and M. Sawai: Synthesis of Ecdysone. III. A Novel Synthesis of I4α-Hydroxy-7-en-6-oxo Steroids. Chem. Pharm. Bull (Japan) 16, 1593 (1968).CrossRefGoogle Scholar
  90. 90.
    Mori, H., K. Shibata, K. Tsuneda and M. Sawai: Synthesis of Ecdysone. V. Synthesis of 22-Isoecdysone. Chem. Pharm. Bull. (Japan) 16, 2416 (1968).CrossRefGoogle Scholar
  91. 91.
    Mori, H., K. Shibata, K. Tsuneda and M. Sawai: Synthesis of Ecdysone. IV. A Novel Synthesis of the Side Chain Structure of Ecdysone. Chem. Pharm. Bull. (Japan) 17, 690 (1969).CrossRefGoogle Scholar
  92. 92.
    Mori, H., K. Shibata, K. Tsuneda, M. Sawai and K. Tsuda: The Configuration of 22-Hydroxycholestero. Chem. Pharm. Bull. (Japan) 16, 1407 (1968).CrossRefGoogle Scholar
  93. 93.
    Mori, H., K. Tsuneda, K. Shibata and M. Sawai: Synthesis of Ecdysone. II. Synthesis of and Stereochemistry of 2β,3β-Dihydroxycholestan-6-ones and Their Derivatives. Chem. Pharm. Bull. (Japan) 15, 466 (1967).CrossRefGoogle Scholar
  94. 94.
    Moriyama, H. and K. Nakanishi: Insect Hormones. VI. Confirmation of the Skeletal Structure of Ponasterone A. Tetrahedron Letters 1968, 1111.Google Scholar
  95. 95.
    Nakanishi, K., M. Koreeda, M.L. Chang and H.Y. Hsu: Insect Hormones. V. The Structures of Ponasterones B and C. Tetrahedron Letters 1968, 1105.Google Scholar
  96. 96.
    Nakanishi, K., M. Koreeda, S. Dasaki, M.L. Chang and H.Y. Hsu: Insect Hormones. I. The Structure of Ponastereone A, an Insect-Moulting Hormone from the Leaves of Podocarpus nakaii Hay. Chem. Commun. 1966, 915.Google Scholar
  97. 97.
    Ohtaki, T.: On the Delayed Pupation of the Fleshfly, Sarcophaga peregrina. Jap. J. Med. Sci. Biol. 19, 97 (1966).Google Scholar
  98. 98.
    Ohtaki, T., R.D. Milkman and C.M. Williams: Ecdysone and Ecdysone Analogues: Their Assay on the Fleshfly Sarcophaga peregrina. Proc. Nat. Acad. Sci. (USA) 58, 981 (1967).CrossRefGoogle Scholar
  99. 99.
    Ohtaki, T., R.D. Milkman and C.M. Williams: Dynamics of Ecdysone Secretion and Action in the Fleshfly Sarcophaga peregrina. Biol. Bull. 135, 322 (1968).CrossRefGoogle Scholar
  100. 100.
    Rimpler, H.: Steroide mit ecdysonartiger Wirkung aus Vitex megapotarnica. Pharmaz. Ztg. 48, 1799 (1967).Google Scholar
  101. 101.
    Rimpler, H.: Pterosteron, Polypodin B und ein neues ecdysonartiges Steroid (Viticosteron E) aus Vitex megapotamica (Verbenaceae). Tetrahedron Letters 1969, 329.Google Scholar
  102. 102.
    Rimpler, H. und G. Schulz: Vorkommen von 20-Hydroxy-ecdyson in Vitex megapotamica. Tetrahedron Letters 1967, 2033.Google Scholar
  103. 103.
    Rufer, C., H. Hoffmeister, H. Schairer und M. Traut: Zur Chemie des Ecdysons, V. Versuche zur Darstellung von Steroid-Δ 7-6-ketonen mit 3.4-Diol-Gruppierung. Chem. Ber. 98, 2383 (1965).CrossRefGoogle Scholar
  104. 104.
    Sato, Y., M. Sakai, S. Imai and S. Fujioka: Ecdysone Activity of Plantoriginated Molting Hormones Applied on the Body Surface of Lepidopterous Larvae. App. Ent. Zool. 3, 49 (1968).Google Scholar
  105. J05.
    Sauer, H.H., R.D. Bennett and E. Heftmann: Ecdysterone Biosynthesis in Podocarpus elata. Phytochem. 7, 2027 (1968).CrossRefGoogle Scholar
  106. 106.
    Shaaya, E. und P. Karlson: Der Ecdysontiter wahrend der Insektenentwicklung II. Die postembryonale Entwicklung der SchmeiBf liege Calliphora erythrocephala Meig. J. Insect Physiol. 11, 65 (1965).CrossRefGoogle Scholar
  107. 107.
    Shaaya, E. und P. Karlson: Der Ecdysontiter wahrend der Insektenentwicklung IV. Die Entwicklung der Lepidopteren Bombyx mori L. und Cerura vinula L. Developmental Biology 11, 424 (1965) and previous references cited therein.CrossRefGoogle Scholar
  108. 108.
    Shibata, K. and H. Mori: Synthesis of Rubrosterone. Chem. Pharm. Bull. (Japan) 16, 1404 (1968).CrossRefGoogle Scholar
  109. 109.
    Siddall, J.B., A.D. Cross and J.H. Fried: Synthetic Studies on Insect Hormones. II. The Synthesis of Ecdysone. J. Amer. Chem. Soc. 88, 862 (1966).CrossRefGoogle Scholar
  110. 110.
    Siddall, J.B., D.H.S. Horn and E.J. Middleton: Synthetic Studies on Insect Hormones. The Synthesis of a Possible Metabolite of Crustecdysone (20-Hydroxyecdysone). Chem. Commun. 1967, 899.Google Scholar
  111. 111.
    Siddall, J.B., J.P. Marshall, A. Bowers, A.D. Cross, J.A. Edwards and J.H. Fried: Synthetic Studies on Insect Hormones. I. Synthesis of the Tetracyclic Nucleus of Ecdysone. J. Amer. Chem. Soc. 88, 379 (1966).CrossRefGoogle Scholar
  112. 112.
    Staal, G.B.: Plants as a Source of Insect Hormones. Proc. Nederl. Akad. Wetenschappen (Amsterdam) Series C 70, 409 (1967).Google Scholar
  113. 113.
    Stamm, M.D.: Estudios sobre Hormonas de Invertebrados II. Aislamiento de Hormonas de la Metamorfosis en el Ortoptero Dociostaurus maroccanus. Anales Real. Soc. Espan. Fis. Quim. (Madrid) 55 B, 171 (1959).Google Scholar
  114. 114.
    Takemoto, T., S. Arihara and H. Hikino: Structure of Ponasteroside A, a Novel Glycoside of Insect-Moulting Substance from Pteridium aquilinum var. latiusculum. Tetrahedron Letters 1968, 4199.Google Scholar
  115. 115.
    Takemoto, T., S. Arihara, Y. Hikino and H. Hikino: Structure of Pterosterone, a Novel Insect-Moulting Substance from Lastrea thelypteris and Onoclea sensibilis. Tetrahedron Letters 1968, 375.Google Scholar
  116. 116.
    Takemoto, T., S. Arihara, Y. Hikino and H. Hikino: Isolation of Insect Moulting Substances from Pteridium aquilinum var. latiusculum. Chem. Pharm. Bull. (Japan) 16, 762 (1968).CrossRefGoogle Scholar
  117. 117.
    Takemoto, T., Y. Hikino, T. Arai and H. Hikino: Structure of Lemmasterone, a Novel C29 Insect-Moulting Substance from Lemmaphyllum microphyllum. Tetrahedron Letters 1968, 4061.Google Scholar
  118. 118.
    Takemoto, T., Y. Hikino, T. Arai, M. Kawahara, C. Konno, S. Arihara and H. Hikino: Isolation of Insect Moulting Substances from Matteuccia struthiopteris, Lastrea thelypteris, and Onoclea sensibilis. Chem. Pharm. Bull. (Japan) 15, 1816 (1967).Google Scholar
  119. 119.
    Takemoto, T., Y. Hikino, T. Arai, C. Konno, S. Nabetani and H. Hikino: Isolation of Insect Moulting Substances from Pleopeltis thunbergiana, Neocheiropteris ensata, and Lemmaphyllum microphyllum. Chem. Pharm. Bull. (Japan) 16, 759 (1968).CrossRefGoogle Scholar
  120. 120.
    Takemoto, T., Y. Hikino, S. Arihara, H. Hikino, S. Ogawa and N. Nishimoto: Absolute Configuration of Inokosterone, an Insect-Moulting Substance from Achyranthes fauriei. Tetrahedron Letters 1968, 2475.Google Scholar
  121. 121.
    Takemoto, T., Y. Hikino, H. Hikino, S. Ogawa and N. Nishimoto: Structure of Rubrosterone, a Novel C19 Metabolite of Insect-Moulting Substances from Achyranthes rubrofusca. Tetrahedron Letters 1968, 3053.Google Scholar
  122. 122.
    Takemoto, T., Y. Hikino, H. Hikino, S. Ogawa: Rubrosterone, a Metabolite of Insect Metamorphosing Substances from Achyranthes rubrofusca: Structure and Absolute Configuration. Tetrahedron 25, 1241 (1969).CrossRefGoogle Scholar
  123. 123.
    Takemoto, T., Y. Hikino, H. Jin, T. Arai and H. Hikino: Isolation of Insect Moulting Substances from Osmunda japonica and Osmunda asiatica. Chem. Pharm. Bull. (Japan) 16, 1636 (1968).CrossRefGoogle Scholar
  124. 124.
    Takemoto, T., Y. Hikino, H. Jin and H. Hikino: Isolation of Ponasterone A from Taxus cuspidata var. nana. Yakugaku Zasshi 88, 359 (1968).Google Scholar
  125. 125.
    Takemoto, T., Y. Hikino, K. Nomoto and H. Hikino: Structure of Cyasterone, a Novel C29 Insect-Moulting Substance from Cyathula capitata. Tetrahedron Letters 1967, 3191.Google Scholar
  126. 126.
    Takemoto, T., Y. Hikino, T. Okuyama, S. Arihara and H. Hikino: Structure of Shidasterone, a Novel Insect-Moulting Substance from Blechnum niponicum. Tetrahedron Letters 1968, 6095.Google Scholar
  127. 127.
    Takemoto, T., K. Nomoto and H. Hikino: Structure of Amarasterone A and B, Novel C29 Insect-Moulting Substances from Cyathula capitata. Tetrahedron Letters 1968, 4953.Google Scholar
  128. 128.
    Takemoto, T., K. Nomoto, Y. Hikino and H. Hikino: Structure of Capitasterone, a Novel C29 Insect-Moulting Substance from Cyathula capitata. Tetrahedron Letters 1968, 4929.Google Scholar
  129. 129.
    Takemoto, T., S. Ogawa, M. Morita, N. Nishimoto, K. Dome and K. Morishima: Studies on the Constituents of Achyranthis Radix. VI. Determination of Insect-Moulting Hormones. Yakugaku Zasshi 88, 39 (1968).Google Scholar
  130. 130.
    Takemoto, T., S. Ogawa and N. Nishimoto: Isolation of the Moulting Hormones of Insects from Achyranthis Radix. Yakugaku Zasshi 87, 325 (1967).Google Scholar
  131. 131.
    Takemoto, T., S. Ogawa and N. Nishimoto: Studies on the Constituents of Achyranthis Radix. II. Isolation of the Insect-Moulting Hormones. Yakugaku Zasshi 87, 1469 (1967).Google Scholar
  132. 132.
    Takemoto, T., S. Ogawa and N. Nishimoto: Studies on the Constituents of Achyranthis Radix. III. Structure of Inokosterone. Yakugaku Zasshi 87, 1474 (1967).Google Scholar
  133. 133.
    Takemoto, T., S. Ogawa, N. Nishimoto, S. Arihara and K. Bue: Insect Moulting Activity of Crude Drugs and Plants. I. Yakugaku Zasshi 87, 1414 (1967).Google Scholar
  134. 134.
    Takemoto, T., S. Ogawa, N. Nishimoto, H. Hirayama and S. Taniguchi: Isolation of the Insect-Moulting Hormones from Mulberry Leaves. Yakugaku Zasshi 87, 748 (1967).Google Scholar
  135. 135.
    Takemoto, T., S. Ogawa, N. Nishimoto, H. Hirayama and S. Taniguchi: Studies on the Constituents of Achyranthis Radix. VII. The Insect-Moulting Substances of Achyranthes and Cyathula. Supplement. Yakugaku Zasshi 88, 1293 (1968).Google Scholar
  136. 136.
    Takemoto, T., S. Ogawa, N. Nishimoto and H. Hoffmeister: Steroide mit Häutungshormon-Aktivität aus Tieren und Pflanzen. Z. Naturforsch. 22b681 (1967).Google Scholar
  137. 137.
    Takemoto, T., S. Ogawa, N. Nishimoto and S. Taniguchi: Studies on the Constituents of Achyranthis Radix. IV. Isolation of the Insectmoulting Hormones from Formosan Achyranthes spp. Yakugaku Zasshi 87, 1478 (1967).Google Scholar
  138. 138.
    Takemoto, T., S. Ogawa, N. Nishimoto, K.-Y. Yen, K. Abe, T. Sato, K. Osawa and M. Takahashi: The Isolation of Ecdysterone from the Radix of Achyranthes obtusifolia Lam. Yakugaku Zasshi 87, 1521 (1967).Google Scholar
  139. 139.
    Takemoto, T., T. Okuyama, S. Arihara, Y. Hikino and H. Hikino: Isolation of Insect Moulting Substances from Blechnum amabile and Blechnum niponicum. Chem. Pharm. Bull. (Japan) 17, 1973 (1969).CrossRefGoogle Scholar
  140. 140.
    Thompson, M.J., J.N. Kaplanis, W.E. Robbins and R.T. Yamamoto: 20,26-Dihydroxyecdysone, a New Steroid with Moulting Hormone Activity from the Tobacco Hornworm, Manduca sexta (Johannson). Chem. Commun. 1967 650.Google Scholar
  141. 141.
    Thomson, J.A., J.B. Siddall, M.N. Galbraith, D.H.S. Horn and E.J. Middleton: The Biosynthesis of Eedysones in the Blowfly Calliphora stygia. Chem. Commun. 1969, 669.Google Scholar
  142. 142.
    Velgová, H., L. Lábler, V. Černy, F. Šorm and K. Sláma: Some Further Compounds Producing Molting Deficiencies in an Insect. Collect. Czech. Chem. Comm. 33, 242 (1968).Google Scholar
  143. 143.
    Wiechert, R., U. Kerb, P. Hocks, A. Furlenmeier, A. Furst, A. Langeman, und G. Waldvogel: Zur Synthese des Ecdysons. Synthesen von 2β,3β-Dihydroxy-6-keto-A/B-cis-Steroiden. Helv. Chim. Acta 49, 1581 (1966).CrossRefGoogle Scholar
  144. 144.
    Williams, C.: The Juvenile Hormone, I. Endocrine Activity of the Corpora allata of the Adult Cecropia Silkworm. Biol. Bull. 116, 323 (1959) and earlier references cited therein.CrossRefGoogle Scholar
  145. 145.
    Williams, C.: Ecdysone and Ecdysone-analogues: Their Assay and Action on Diapausing Pupae of the Cynthia Silkworm. Biol. Bull. 134, 344 (1968).CrossRefGoogle Scholar

Copyright information

© Springer-Verlag/Wien 1970

Authors and Affiliations

  • Hiroshi Hikino
    • 1
  • Yasuko Hikino
    • 1
  1. 1.SendaiJapan

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